Journal
RUSSIAN CHEMICAL BULLETIN
Volume 53, Issue 12, Pages 2768-2773Publisher
SPRINGER
DOI: 10.1007/s11172-005-0188-5
Keywords
triarylboroxine; terphenyl; 4-bromophenylferrocene; cross-coupling; X-ray diffraction analysis
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The reaction of 4-bromophenylferrocene with butyllithium followed by treatment of the organolithium compound with tributyl borate afforded tris(4-ferrocenylphenyl)boroxine (2). X-ray diffraction study of the solvate 2(.)2C(6)H(6) revealed an intermolecular stacking interaction between the boroxine ring and the Cp rings in the crystal structure. Cross-coupling of compound 2 with 4'-bromo-4-nitro-1,1'-biphcnyl produced 4-ferrocenyl-4-nitro-1,1':4',1-terphenyl (3). X-ray diffraction study of terphenyl 3 showed that this compound crystallizes in the noncentrosymmetric space group P2(1). In the crystal, molecules 3 are packed in an antiparallel head-to-tail fashion, which is unfavorable for generation of strong nonlinear optical effects.
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